RedBird Capital owns AC Milan, a Formula One team, and — through Fenway — Liverpool FC and the Boston Red Sox. It also owns a sports insurance business that doesn't cover any of this.

Bishop Street Underwriters has been buying into American amateur sport since 2023: nine operating companies now, $650m of premium last year, $800m targeted this year. Jim Arnold and George Wilson run its sports and entertainment division. On why you buy two competitors and use each to fix the other's weakness, what a founder-friendly sponsor does differently with a family business, and why flag football is now one of the more interesting underwriting problems in the market.

Guests: Jim Arnold, President of Sports & Entertainment (previously with Guy Carpenter and Markel) and George Wilson, SVP and Head of Distribution (previously with RT Specialty, AIG, and Great American) at Bishop Street Underwriters.

• 00:05 — Introduction
• 01:47 — "You must insure Messi and LeBron. Now tell us what you actually do."
• 03:01 — The size of the youth sports market
• 03:50 — Jim Arnold: law, claims, Markel, and why operations
• 05:13 — George Wilson: "I don't want to sell and I don't want to be involved in insurance"
• 07:06 — Bishop Street: nine operating companies in three years
• 08:22 — Why a panel of carriers rather than one balance sheet
• 09:13 — F.L. Dean, SportUnderwriters.com, SportsCanadaUnderwriters.com
• 10:17 — The mirror image: what each agency base asked for
• 12:15 — "We acquired literally John Dean"
• 12:50 — Why both brands survive
• 13:36 — What the RedBird and Weatherford connection delivers
• 15:26 — AI at the submission, not at the decision
• 16:27 — Emerging sports, and underwriting with no loss history
• 17:53 — The centralisation opportunity in governing bodies
• 18:32 — What private equity brings

• Bishop Street / White Mountains, $125m investment
• "Bishop Street plots next moves," Program Manager, June 2026
• RedBird / Weatherford launch Collegiate Athletic Solutions

Follow the Fortunes covers the risk behind the return in sport. Hosted by Phil Schmidt.

Views expressed by guests are their own. Nothing here is insurance, investment or legal advice.

The capital moving through sport, and risk it's exposed to. Host Phil Schmidt talks with the investors, owners, executives, and underwriters doing the deals — where the money comes from, what can go wrong, and who carries it.